(S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine

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Cat Number

INT1110767980

CAS Number

1110767-98-0

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Product Detail Description Customer Q&A

CAS Number

1110767-98-0

Storage

2-8℃

Synonyms

4-(3-((S)-1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine

Molecular Formula

C18H26N2O2S

Molecular Weight

334.48

Smiles

S1C=C(C2=CC=CC([C@@H](OCCCCCC)C)=C2OC)N=C1N

Appearance

White to off-white solid

Boiling Point

462.4℃

Relative Density

1.105

pKa

4.3

General Description

(S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine is a complex, chiral thiazole derivative that functions as a high-value pharmaceutical intermediate. This molecule is characterized by a central thiazole-2-amine core substituted with a specifically functionalized phenyl ring. The presence of a hexyloxy-modified chiral side chain and a methoxy group provides unique structural attributes that are essential for the pharmacological activity and target specificity of advanced therapeutic agents

Mechanism of Action

As a synthetic scaffold, (S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine is designed to serve as a key building block in the development of selective enzyme inhibitors or receptor modulators. The thiazole-2-amine moiety is a privileged structure in medicinal chemistry, capable of participating in critical hydrogen-bonding interactions within the active sites of proteins. The bulky hexyloxy-ethyl side chain and the methoxy-substituted phenyl ring are strategically positioned to optimize binding pocket occupation and lipophilic interactions.

Application

(S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine is primarily utilized in the pharmaceutical industry as an intermediate for synthesizing innovative active pharmaceutical ingredients (APIs) targeting metabolic disorders, inflammatory conditions, and neurological diseases. It is frequently employed in medicinal chemistry research for the construction of diversified compound libraries intended for high-throughput screening.

What is the role of the thiazol-2-amine core in (S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine?

The thiazol-2-amine core in it is a privileged heterocyclic structure that facilitates crucial hydrogen-bonding interactions with biological targets, enhancing its potency.

How does the (S)-chiral side chain influence the biological function of (S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine?

The (S)-chiral side chain in it provides specific three-dimensional geometry, which is essential for ensuring high-affinity, enantioselective binding to receptors or enzymes.

Is (S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine soluble in common organic solvents?

Yes, it exhibits excellent solubility in typical medicinal chemistry solvents such as dichloromethane, dimethyl sulfoxide (DMSO), and methanol.

What is the primary industrial application for (S)-4-(3-(1-(hexyloxy)ethyl)-2-methoxyphenyl)thiazol-2-amine?

It is primarily used as a key pharmaceutical intermediate for the synthesis of advanced APIs, particularly those aimed at regulating complex metabolic and inflammatory pathways.